Tributylstannane → HCID 12151499, compound

HRID 434175Notes

Reaction equation

HRID 434175 reaction equation
[SnH](CCCC)(CCCC)[CH2:2][CH2:3][CH2:4]C.CC(N=NC(C#N)(C)C)(C#N)C.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27]1>C1C=CC=CC=1>[CH:3]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27]1)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 10328Indoline

Product 1

HCID 12151499HCID 12151499, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A three-hour addition of nBu3SnH (154 μL, 573 μmol) and AIBN (34 mg, 208 μmol) solution in benzene (1 mL) to a refluxing solution of the unpurified ketimine (125 mg, 521 μmol) in benzene (50 mL) delivered, after flash chromatography (30% CH2Cl2 Hexanes) 0.024 g (30%) of the desired indoline as a colorless oil. Rf=0.1 (30% CH2Cl2 Hexanes); IR (film) 3047, 1607 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.04 (t, J=6.7 Hz, 2H), 6.59 (t, J=7.4 Hz, 1H), 6.42 (d, J=8.1 Hz, IH), 3.83 (sep, J=6.6 Hz, 1H), 3.33 (t, J=8.5 Hz, 2H), 2.93 (t, J=8.3 Hz, 2H), 1.15 (d, J=6.7 Hz, 6H); 13C NMR (100 MHz, CDCl3) ppm 151.5, 130.5, 127.5, 124.6, 117.1, 107.3, 46.0, 45.7, 28.4, 18.4; HRMS (EI) Exact mass calcd for C11H15N [M]+, 161.1204. Found 161.1201.

Sources & evidence

ORD record
ord-d731ee8c1259441c8d689cd3412b95b4
Source dataset
uspto-grants-2003_12
Patent number
US06670479B2

Reaction notes

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